When I was in college, I was too broke to buy decent fonts. I knew that I could either approach every project with my limited number of typefaces, spend days digging through terrible free font websites to find anything even remotely acceptable, or “draw my own fonts” (I say this in quotes because it’s a complete misuse of the word font—a mistake I made all the time when I was younger). I noticed that the more I “drew fonts” for my own projects, the more I lettered titles and logotypes and headlines for fake magazines, the more my work started to stand out from my classmates. Everything felt more personal and more cohesive. Plus I loved to do it! My student portfolio ended up having a fair amount of lettering in it which was ultimately why Louise Fili ended up hiring me.

While I was working for Louise I really fell in love with lettering (note the proper terminology now). All day every day I drew words and phrases for her. I lettered for logotypes and book covers, magazine headlines and pretty packaging. While working for Louise I would work on freelance illustration. More and more I started to incorporate lettering into my freelance editorial illustration work—at first just as a component within the illustration, and over time I would offer conceptual solutions that were entirely lettering based. More and more people started to notice the lettering work and I began being hired just to do lettering.

The real lesson I learned was that in order to do what you want for a living, all you have to do is find a way to show people that you do it. If you want to be a book cover designer but don’t have a single book cover in your portfolio, the chances of you getting hired to design book covers is very low. You have to put the pieces in your portfolio that reflect the work you want to be doing.

Lettering takes a ton of practice and I was able to learn under one of the best, but ultimately if I didn’t take the initiative to make lettering a part of all work I was doing, I wouldn’t be a letterer now.

For illustration work and lettering work, I always start with pencil sketches—not because it is my preferred way to work, but because clients need to approve something before I can move to final. My pencils used to be quite rough but because I’ve been doing more and more lettering work for advertising clients, they’ve become more refined. After a sketch is approved, I jump into illustrator, usually not tracing my sketch for the final. I believe that the translation from sketch to final without tracing helps me correct my mistakes as I go. I idealize like how you would if you were drawing a person from memory versus from real life.

I don’t use a lot of fancy tricks in illustrator, mostly just the pen tool. After a few years of working intensely with the program it has become more natural for me to work on the computer than by hand. I don’t use a wacom tablet (I hold a pen like a child holds a crayon (in a tight fist that will only catalyze the carpal tunnel)), just a mouse or the trackpad on my laptop. I usually work with the grid on at first, starting with a single weight line and then adding thickness or ornament later depending on what I’m trying to achieve. I make general decisions at the beginning to figure out what kind of lettering I want to draw (a script? slanted or upright? thick or thin? sans serif? retro feeling or more modern feeling?) and then add decoration / ornamentation after the “skeleton” is drawn.

Lettering is essentially illustrations of letters, words, and phrases. As a letterer, when I’m hired to draw the word “holiday” I don’t first draw the entire alphabet in the style I wish, then position the letters to spell out the word. I draw the word as a unique image. This means that in a lot of lettering, if you rearrange the letters it would look pretty crappy—it’s meant to be seen and used in that configuration and that configuration only.

Typeface designers work very differently. They have to create a system of letters that can be endlessly rearranged and work together. Display typefaces are usually less elaborate than text typefaces (though they look more elaborate, by and large text typefaces are much more difficult to make). Type designers have to make typefaces that even the least design-savvy person can work with and set beautifully. They create software that you can essentially own forever without updating. I try to advocate for typeface designers as much as I can because most designers don’t stop to think about the work that goes into making fonts. They make what I do seem easy!